2(5H)-Furanone, 4-methoxy-5-(methoxyphenylmethylene)-, (E)-

Base Information

• Chemical Name: 2(5H)-Furanone, 4-methoxy-5-(methoxyphenylmethylene)-, (E)-
• CAS No.: 78819-24-6
• Molecular Formula: C13H12O4
• Molecular Weight: 232.232
• Mol file: 78819-24-6.mol

Synonyms:2(5H)-Furanone, 4-methoxy-5-(methoxyphenylmethylene)-, (E)-;78819-24-6

Chemical Property of 2(5H)-Furanone, 4-methoxy-5-(methoxyphenylmethylene)-, (E)-

Chemical Property:

• Vapor Pressure: 1.32E-07mmHg at 25°C
• Boiling Point: 430.3°C at 760 mmHg
• Flash Point: 194.8°C
• Density: 1.23g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 232.07355886
• Heavy Atom Count: 17
• Complexity: 362

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=O)OC1=C(C2=CC=CC=C2)OC
• Isomeric SMILES: COC\1=CC(=O)O/C1=C(\C2=CC=CC=C2)/OC

Technology Process of 2(5H)-Furanone, 4-methoxy-5-(methoxyphenylmethylene)-, (E)-

There total 13 articles about 2(5H)-Furanone, 4-methoxy-5-(methoxyphenylmethylene)-, (E)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.7%

methyl 5-(1-methoxybenzyl)tetronate (82204-21-5) → (Z)-4-methoxy-5-benzylidenefuran-2(5H)-one (72031-58-4) + 5,6-Z-fadyenolide (78819-23-5) + 5,5-E-fadyenolide (78819-24-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 10h; Yields of byproduct given; Heating;

Reference yield:

methyl 5-(1-methoxybenzyl)tetronate (82204-21-5) → 5,5-E-fadyenolide (78819-24-6)

Guidance literature:

Multi-step reaction with 3 steps

1: n-BuLi / -78 °C

2: Br₂ / -78 °C

3: 0.162 g / various solvent(s) / -78 deg C, 2 h, then RT_.

With n-butyllithium; bromine; In various solvent(s);

Reference yield:

methyl thiobenzoate (5873-86-9) + C5H5O3(1-)*Na(1+) → 5,6-Z-fadyenolide (78819-23-5) + 5,5-E-fadyenolide (78819-24-6)

Guidance literature:

C₅H₅O₃^(1-)*Na⁽¹⁺⁾; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

methyl thiobenzoate; With methyl iodide; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

With sodium hexamethyldisilazane; In tetrahydrofuran; for 2h; Overall yield = 62percent; Overall yield = 144 mg; stereoselective reaction; Inert atmosphere; Reflux;

DOI:10.1021/acs.joc.0c02502

upstream raw materials:

5,6-Z-fadyenolide

methyl 5-(1-methoxybenzyl)tetronate

5-Bromo-4-methoxy-5-(methoxy-phenyl-methyl)-5H-furan-2-one

4-methoxy-5H-furan-2-one

Refernces

• 1、 Pelter, Andrew,Al-Bayati, Redha I. H.,Ayoub, Miqdad T.,Lewis, Wynn,Pardasani, Pushpa,Hansel, Rudolf. "Synthetic Routs to the Piperolides, Faydenolides, Epoxypiperolides, and Related Compounds". . p. 717 - 742. Retrieved 2007/10/02.